What's the best, safest way to ask someone you work with on a date? (We definitely have a connection)?

Question

I have a strong, flirtatious connection with someone I work with, all the signs are there, and I'd love to see how things could develop, but it's still a little awkward to make an approach given the work context. How should I broach the issue?

Answer 1

First, I'm assuming there are no work relating implications for the two of you dating.



I usually find suggesting an activity you share an interest in to be the easiest way to move things to the next level. It gets you outside of the office-relationship context while it is still safer than something much more obvious like a fancy dinner. Something you would be interested in doing is also a sure bet to make sure the first date is fun without having to depend on office-connection smoothly translating to a new environment. And while I'm sure she will be somewhat aware of your intentions, most people enjoy dating a little more when there isn't the added pressure of both of you having to be VERY aware that you are evaluating each other for further dates.



If you are both interested in say dancing, theatre, or rock-climbing mention a club, performance, or climb spot you were interested in checking out and then casually suggest that you should to it together sometime. If you want to be very cautious, you coul d make an extra point of making it seem like the the suggestion was entirely spontaneous.

Answer 2

When entering into any new romance project, I think it is really important to model all the possible outcomes in as much detail as possible. You need to collect your base assumptions (not married, dating, etc.) and then apply all your variables to these assumptions to make sure you get the outcome you want. I also find that sometimes writing these down, perhaps in Powerpoint, is a valid way to formalise and present your thoughts to the object of your desires. Let us know how you get on.

Answer 3

Don't just dive in there, buid things up gradually with a few compliments first, like commenting on how nice a new haircut looks

Answer 4

Note: in case you are a Yahoo employee, I believe that company policy forbids dating among employees.

Answer 5

Two words - Christmas party

Answer 6

Add her to messanger and start a good coversation.